Lab 10 - Gaurav Singh Brooke Leslie/Chad Landrie 22...

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Gaurav Singh Brooke Leslie/Chad Landrie 22 Wednesday 2009 Lab Ten : Stereospecific Ni-Catalyzed Hydrogenation of Ethyl 3-Oxytnoate to Ethyl cis-3- Octenoate Introduction: The key purpose of this experiment is to investigate methods for producing biodiesel by using Lewis-acid catalysts. Biodiesel can be a potential alternative fuel source if it can efficiently be mass-produced; it is derived from biological sources instead of its nonrenewable counterpart petroleum—which is derived from fossil sources and is a mixture of hydrocarbons. This is significant because biodiesel has fewer deleterious implications on the environment. The substance is not toxic and biodegradable; additionally, it has more oxygen which eliminates the need for addition of oxygen. It also does not contain any sulfur (reducing pollution) and it releases more energy when it is combusted and thereby has greater efficiency. Biodiesel contains esters of fatty acids, which are derived from triglycerides. A triglyceride contains three ester groups, and is an ester as well. The conversion of triglycerides into methyl esters is called transesterification. The efficiency of this process determines whether biodiesel can be as sustainable as petrodiesel and thus replace it in the future. Industrial methods to do this process use alkaline catalysts, but this is not ideal because of the formation of soap, a by-product which reduces the efficiency at which biodiesel is produced.
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One of biodiesel’s key drawbacks is an increase in nitrous oxide emissions. The chemical composition of biodiesel is a likely cause of this phenomenon; the amount of unsaturation (alkenes) in the hydrocarbon side chains may be to blame. To investigate whether the side chain double bonds are responsible for this, they must be isolated and then burned in a shock tube. But since this can’t be done for some fatty acid methyl esters because they do not have a large enough equilibrium vapor pressure, substitutions are used. However, compound 10 is not commercially available, so it’s vital to synthesize compound 14 through a two step sequence. This is the overall purpose of labs nine and ten. This lab, specifically, prepares compound 14 from compound 13 (which was created in the last lab). The reaction is diagrammed in figure one, below. A supposed process for the way this happens, via a catalyst metal surface, is shows in figure two. Results from TLC and IR indicate that the expected product was in fact formed. HNMR results indicate that the cis-alkene was formed. The successful completion of this project
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Lab 10 - Gaurav Singh Brooke Leslie/Chad Landrie 22...

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